JPH05252974A - Production of turanose and its use - Google Patents

Abstract

PURPOSE:To obtain in an industrially advantageous way, turanose having refined and good-quality sweetness by making cyclomaltodextrin glucanotransferase act on an aqueous solution containing a starch substance and fructose followed by collecting the product. CONSTITUTION:A starch substance (e.g. dextrin) and fructose are dissolved in hot water and the pH level of the solution is adjusted to 5.6, and cyclomaltodextrin glucanotransferase derived from Bacillus stearothermophilus or saccharifying alpha-amylase is added to the resultant solution at 60 deg.C to carry out reaction to form turanose, followed by heating to deactivate the enzyme. Then, the resulting liquor containing the turanose formed is conventionally decolored using active carbon and put to a column chromatography using a salt-type strongly acidic cation exchange resin to effect purification into a liquor of high turanose content, which is, in turn, concentrated and crystallized; the crystal produced is collected, thus obtaining the objective turanose with refined and good-quality sweetness.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing turanose and its use. More specifically, it is prepared by reacting starch and fructose with cyclomaltodexrin glucanotransferase or a saccharified α-amylase to produce turanose. , A method for producing turanose, which is characterized by collecting the same, and a food or drink containing the turanose,
The present invention relates to compositions such as cosmetics and pharmaceuticals.

[0002]

BACKGROUND OF THE INVENTION Turanose has long been known as a disaccharide represented by the formula: 3-O-α-D-glucopyranosyl-D-fructose. This sugar is present in the natural world such as pine needles and honey, has a sweet taste, is easily soluble in water,
It is expected that it can be advantageously used for oral beverages such as various beverages, processed foods, and favorite foods.

A method of producing turanose is disclosed in, for example, Eugene Paesu's Method in Carbohydrate Chemistry (Met).
hods in carbohydrate chem
ISTRY), pp. 353-357, (1962)
Is prepared by acidolysis of melezitose as described in. According to this report, melezitose (300
A small amount of sulfuric acid was added to the 19% aqueous solution of g) and kept in a boiling water bath for 15 minutes. After neutralization, yeast was added to the resulting glucose- and turanose-containing solution to remove glucose by fermentation, and then purified and concentrated. Then, methanol was added to the obtained syrup to obtain 187 g of crystals of turanose. According to this method, the yield based on the raw material melezitose is as high as 60% or more.

[0004] However, although it is known in the natural world that the raw material, meletitose, is contained in the nectar secreted by aphids, it is extremely difficult to industrially produce turanose from this raw material. In addition, as a biochemical production method for turanose, Chiba et al. Have used Agricultural and Biological Chemistry (Ag.
critical and Biological
Chemistry) Volume 35, 1292 to 1
297, (1971).

According to this report, α-derived from brewer's yeast
It has been shown that a small amount of turanose is produced together with maltulose by allowing glucosidase (EC 3.2.1.20) to act on a mixed solution of phenyl-α-glucoside and fructose. This method is also difficult to obtain a large amount of phenyl-α-glucoside, in addition,
Since the desired amount of turanose is low, it is unsuitable as an industrial production method. In addition, Okada et al.
No. 251, and Hirao et al.
No. 0, in a mixed solution of starch liquefaction liquid and fructose, Bacillus maceras.
It is disclosed that by reacting the enzyme (ns), oligosaccharide mixtures having various degrees of polymerization in which fructose is bound to the reducing end of the oligosaccharide molecule are produced.

However, the structure of the transition product has not been clarified. As described above, the industrial mass production method of turanose has not been established, and only a reagent as a standard substance is commercially available, and it has not yet been used for food and drink, cosmetics, pharmaceuticals, etc. ..

[0007]

It is desired to establish a safe, easy and high-yield industrial method for producing turanose and its use.

[0008]

Means for Solving the Problems The present inventor has conducted earnest research with the aim of establishing an industrial production method of turanose and its use. As a result, by reacting cyclomaltodextrin-glucanotransferase or saccharified α-amylase with an aqueous solution containing starch and fructose, turanose is produced, and turanose can be easily produced by collecting it. The present invention has been completed, and the present invention has been completed by establishing compositions of foods, drinks, cosmetics, pharmaceuticals, etc., containing this turanose.

As the starch used in the present invention, starch or a partially decomposed product thereof, which is usually DE 70 or less, is suitable. For example, gelatinized starch, liquefied starch, soluble starch, partially decomposed starch, Are used as appropriate. As the raw material starch, underground starch such as potato starch, tapioca starch and sweet potato starch, and above-ground starch such as corn starch, wheat starch and rice starch are appropriately adopted.

The partially degraded starch is selected from not only amylose, dextrin and cyclomaltodextrin but also maltose, maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose and maltooctaose. 1
One kind or two or more kinds of maltooligosaccharides are also appropriately adopted.

Commercially available fructose is appropriately used. If necessary, fructose contained in isomerized sugar or the like can be used. Cyclomaltodextrin glucanotransferase (EC 2.4.
1.19) is a known Bacillus
Enzymes derived from microorganisms belonging to the genus s), the genus Klebsiella, etc. are appropriately used.

Glycated α-amylase (EC 3.2.
1.1), for example, Bacillus
s) Enzymes derived from microorganisms belonging to the genus etc. are used. The transglycosylation reaction method may be any method capable of producing turanose, and is appropriately selected depending on the enzyme used. For example, when using cyclomaltodextrin glucanotransferase derived from a microorganism belonging to the genus Bacillus,
The enzyme may be allowed to act on the aqueous solution containing starch and fructose in an amount of 1 to 1000 units, preferably 50 to 500 units, per gram of starch solids to produce turanose.

In this case, the weight ratio of starch to fructose is usually 0.1 to 100 times, preferably 0.
2 to 20 times is preferable. Starch concentration is 1 to 70
W / W% (hereinafter, W / W% is abbreviated as% in the present specification unless otherwise specified), preferably 20 to 60%, temperature 20 to 80 ° C., pH 3 to 9, reaction time 1 The reaction may be performed under conditions selected from 100 to 100 hours. If necessary, the enzyme may be further immobilized and repeatedly used. In addition, in the thus obtained reaction liquid containing turanose, glucoamylase or β
-By reacting with amylase, turanose, α-
It is also possible to accumulate glucosyl turanose and the like.

The turanose-containing solution produced by the enzyme reaction as described above usually contains about 1% to 45% of turanose per solid matter, and this is used in a liquid state after being filtered and purified. It is also possible to concentrate and use in the form of syrup, and further to use in the form of solid after drying. Generally, in order to utilize the characteristics of turanose, the solution containing turanose is further separated and purified to be used as a high content of turanose.

The method is, for example, a yeast fermentation method,
A method for separating and removing contaminant saccharides by a membrane filtration method, a fractional precipitation method, a crystallization method, a column chromatography or the like can be appropriately adopted. In particular, JP-A-58-23799,
The method of removing the contaminating saccharides and collecting the fraction containing a large amount of turanose by column chromatography using a salt-type strongly acidic cation exchange resin disclosed in JP-A-58-72598 and the like can be advantageously carried out. At this time, any of the fixed bed system, the moving bed system, and the simulated moving bed system may be adopted. Further, it is optional to concentrate the thus-obtained high-concentration solution of turanose into a high-concentration solution to produce crystalline turanose.

The method for producing crystalline turanose is usually
The degree of saturation is about 1.05 to 2.0, and more specifically, the sugar having a turanose content of 50% or more per solid is made into a solution having a concentration of about 60% to 95%, and the solution temperature is frozen. And at a temperature below the crystalline melting point, eg about 1
It may be crystallized at 0 to 120 ° C.

The crystallization method is usually 40 to 100.
Take a solution of supersaturated Tranose at a relatively high temperature of ℃ in a auxiliary crystal can, and preferably add 0.1 to 20% of seed crystal to the auxiliary crystal can and slowly cool it with slow stirring to promote crystallization and prepare a musket. do it. The crystalline turanose can be produced from the crystallized musket as long as the crystalline turanose can be collected, and for example, known methods such as a syrup method, a block pulverizing method, a fluidized granulation method, and a spray drying method may be adopted.

For example, the honey separation method is a method in which a musket is put into a basket type centrifuge to separate the crystalline turanose and the honey, and it is easy to wash the crystals by spraying a small amount of cold water, if necessary. It is suitable for producing higher purity crystalline turanose. The other three methods are
Since honey is not separated, it is not possible to expect an improvement in the purity of turanose in the obtained honey crystals, but it has the feature of high product yield. Therefore, these products contain various sugars as a honey component other than crystals. This component contains fructose used as a raw material, a starchy substance, and starch decomposition products such as glucose, maltose, and maltotriose.

In the case of the block pulverization method, usually, a mass kit having a concentration of 75 to 95% and a crystallization rate of 10 to 60% is allowed to stand for 0.5 to 5 days to crystallize and solidify the whole as a block. This is crushed or crushed by cutting or the like, and dried to obtain a hardly hygroscopic crystal powder containing honey. In the case of the spray drying method, the concentration is usually 65% to 80%,
A mass kit having a crystallization rate of about 20 to 40% is sprayed, dried with hot air at a temperature at which crystals do not melt, for example, 60 to 100 ° C., and then hot air at 30 to 60 ° C. for about 1 to 20.
Aging is performed for a time to obtain a hardly hygroscopic crystal powder containing honey.

The physicochemical properties such as the melting point and the specific optical rotation of these molasses-containing crystals change depending on the difference in the turanose content per solid. Usually, as the content of turanose decreases, the melting point decreases and the melting temperature range widens. Also, its hygroscopicity increases as the turanose content decreases.

The turanose of the present invention is refined and has a good sweetness. Also, by ingestion, it is digested and absorbed,
Used as a calorie source. Further, it can be used as a sweetener that is unlikely to cause tooth decay because it is hardly fermented by tooth decay-inducing bacteria. Further, since it is a high-quality sweetener, it can be advantageously used as a sugar-coating agent for tablets in combination with a binder such as pullulan or hydroxyethyl starch. Further, it has properties such as osmotic pressure controllability, shaping property, luster imparting property, moisturizing property, viscosity, crystallization preventing property of other sugars, and difficult fermentation property.

These various properties of turanose can be advantageously used in various compositions such as foods and drinks, favorite foods, feeds, cosmetics and pharmaceuticals. Turanose can be used as it is as a seasoning for sweetening. If desired, one or two of the other sweeteners such as, for example, starch syrup, glucose, maltose, sugar, isomerized sugar, honey, maple sugar, sorbitol, dihydrochalcone, stevioside, α-glycosyl stevioside, rebaudioside, etc. May be used by mixing with the appropriate amount above,
If necessary, they can be used by mixing with a bulking agent such as dextrin, starch, lactose and the like.

Further, the turanose powder product is as it is,
If necessary, it may be mixed with a filler, an excipient, a binder and the like and molded into various shapes such as granules, rods, spheres, plates and tablets for use.

The sweetness of turanose is in good harmony with various substances having other tastes such as sourness, salt, taste, astringency, umami, and bitterness. Further, it can be advantageously used for quality improvement. For example,
It can be advantageously used as various seasonings such as soy sauce, miso, vinegar, sauce, mayonnaise and mirin. Also, various Japanese sweets,
Advantageous for sweetening, improving taste and improving quality of various foods and drinks such as Western confectionery, frozen desserts, syrups, pastes, processed foods of vegetables, pickles, meat products, fish products, alcoholic beverages, soft drinks, etc. Available for

It can also be used as feed for domestic animals such as domestic animals. Further, it can be advantageously used as a sweetening agent for various compositions such as cosmetics such as lipsticks, cigarettes, troches, oral liquids, pharmaceuticals, etc. for sweetening, improving taste and improving quality.

The composition of the present invention may be turanose alone, but usually, together with turanose, other substances depending on the purpose, for example, nutritional substances such as proteins, amino acids, lipids, vitamins and minerals, or antibacterial substances are used. Substances, enzymes,
It is manufactured by containing one or more selected from medicinal substances such as hormones and cytokines. At this time, the turanose content is not particularly limited, but it is usually 1% or more, preferably 2% or more,
It is preferable to take advantage of the properties of turanose.

If desired, it is also possible to use one or more other suitable substances, such as one or more of a flavoring agent, a coloring agent, a flavoring agent, a stabilizer, a bulking agent, an excipient and the like. It is optional to shape the resulting composition into an appropriate shape depending on the purpose. The composition thus obtained can be used orally or parenterally.

The method of incorporating turanose in the composition may be such that it is included in the steps until the product is completed. For example, mixing, kneading, dissolving, melting, dipping, spraying, coating, coating, spraying, pouring, A known method such as crystallization or solidification is appropriately selected. Hereinafter, the turanose of the present invention will be described experimentally.

[0029]

[Experiment] Preparation of Turanose and its physicochemical properties

[0030]

[Experiment 1] 25 parts by weight of α-cyclodextrin (sold by Hayashibara Biochemical Laboratories) and commercially available fructose 2
Dissolve 5 parts by weight of water in 50 parts by weight and add 60 parts of this solution.
After adjusting the temperature to 60 ° C and pH 6.0, add Bacillus stearothermophilus-derived cyclomaltodextrin glucanotransferase (Hayashibara Biochemical Laboratories Co., Ltd.) 300 units per α-cyclodextrin glam and react for 20 hours. And then heated to 100 ° C. for 30 minutes to inactivate the enzyme.

This solution was adjusted to pH 4.5 and 55 ° C., and 20 units of glucoamylase (Nagose Seikagaku Kogyo Co., Ltd., trade name Glucozyme) was added per gram of solid matter.
The reaction was allowed to proceed for a period of time and then heated to 100 ° C. for 15 minutes to inactivate the enzyme. Figure 1 shows the gas chromatogram of this solution.
It was shown to. In FIG. 1, the vertical axis indicates the FID (FrameI
The horizontal axis represents time. This solution contained about 40% of turanose based on the solid matter. This solution is decolorized with activated carbon, desalted with an ion exchange resin (H-type and OH-type), purified, concentrated to a concentration of about 40%, and subjected to column chromatography using a fractionation resin. The high content fraction was collected. As the fractionating resin, a salt type strong acid cation exchange resin (sold by Organo Co., Ltd., trade name Amberlite XT-1016Na type) was used, and it was packed in a water-suspended state in a jacketed stainless steel column having an inner diameter of 5.4 cm. ..

At this time, four columns each having a resin layer length of 5 m were continuously arranged so that the total length of the resin layer was about 20 m. While maintaining the temperature in the column at 55 ° C, a raw sugar solution having a concentration of about 40% was added to the resin at 5 v / v%, and then warm water at 55 ° C was added to S.
Fractionation was carried out at a flow rate of V0.3 to collect a fraction containing a large amount of turanose. The concentration of the resulting high-concentration turanose was 75
%, Methanol was added thereto, and the mixture was allowed to stand at 20 ° C. overnight, and crystals were precipitated.

The crystals were dehused and the crystals were washed by spraying a small amount of water to obtain turanose crystals having a purity of 97.9%. Further, this crystal was dissolved in a small amount of water, the above-obtained crystal was added as a seed crystal, allowed to stand overnight at 20 ° C. to crystallize and crystallize, and a turanose crystal having a purity of 99.9% was collected. did.

[0034]

[Experiment 2] Physicochemical properties were investigated using a high-purity crystal sample of turanose prepared by the method of Experiment 1.

(1) Elemental analysis measured value C = 42.05% H = 6.50% O = 5
1.54% Theoretical value C = 42.10% H = 6.48% O = 5
1.42% (molecular formula: C ₁₂ H ₂₂ O ₁₁ , molecular weight 342.3)

(2) Melting point 156.0 to 157.0 ° C. Literature value: 157.0 ° C. (The above-mentioned report by Eugene Patz)

(3) Specific optical rotation [α] D ²⁰ +76.5 to 77.5 ° (C = 1, H ₂
O) Reference value: + 75 ° (C = 3.9, Water) (reported by Eugene Patz mentioned above.)

(4) Ultraviolet absorption No characteristic absorption is shown when measured in an aqueous solution.

(5) Infrared absorption 2 mg of a crystal standard and 200 mg of dry KBr were stirred and mixed to prepare a transparent tablet (thickness: about 0.6 mm),
The infrared absorption spectrum was measured. The result is shown in FIG. This spectrum was in good agreement with the infrared absorption spectrum of commercially available standard Tranose.

(6) Coloring reaction A green color is obtained by the anthrone-sulfuric acid reaction. Red color with cysteine-carbazole sulphate. Felissog's liquid reduction reaction is positive. Iodine reaction is negative.

(7) Physical properties, color of substance It is a colorless and transparent crystal having a true specific gravity of 1.59. The fine crystals are white powder and have a sweetness of about 1/3 that of sucrose. The taste is refined, good and has no odor. It is not hygroscopic and does not deliquesce.

(8) Constituent sugar (a) When hydrolyzed with 1N-sulfuric acid, D-glucose 1
To produce 1 mole of D-fructose. (B) By the action of α-glucosidase, D-glucose and D-fructose are produced. (C) It is not decomposed by the action of β-glucosidase.

(9) Powder X-Ray Diffraction X-ray diffraction was carried out using an X-ray diffractometer (Rigaku Denki Co., Ltd., trade name Geiger Flex RAD-IIB, using CuKα rays). Break angle (2θ)
Are 14.5 °, 19.2 °, 20.1 ° and 20.
8 ° was given. This result was in good agreement with the powder X-ray diffraction pattern of commercially available standard Tranose. FIG. 3 shows a powder X-ray diffraction pattern of this substance.

From the above results, the substance is turanose,
It was determined to be of formula: 3-O-α-D-glucopyranosyl-D-fructose.

[0045]

[Experiment 2] Acute toxicity test When 7-week-old DD mice were used to orally administer high-purity turanose prepared by the method of Experiment 1, an acute toxicity test was conducted, and no deaths were observed up to 5 g. Further administration was difficult. Therefore, the toxicity of this substance is extremely low.

The method for producing turanose of the present invention is shown in Example A, and the use of turanose is shown in Example B.

[0047]

Example A-1 2.5 parts by weight of fructose and 2.5 parts by weight of dextrin (DE18, sold by Matsutani Chemical Industry Co., Ltd., trade name Paindex # 4) were dissolved in 5 parts by weight of water by heating, and this solution was adjusted to pH 5 6. Adjust the temperature to 60 ° C, and use cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus (sold by Hayashibara Biochemical Laboratories, Inc.) at 30 per dextrisogram.
0 unit was added and the reaction was carried out for 20 hours, followed by heating to inactivate the enzyme. This solution was decolorized with activated carbon, desalted with an ion exchange resin (H type and OH type) and purified according to a conventional method, and concentrated to give syrup having a concentration of about 75% at a solid yield of about 93%. Obtained. This product contains about 20% of turanose per solid matter, has an elegant sweetness, an appropriate viscosity and a moisturizing property, and can be advantageously used for various compositions such as food and drink, cosmetics and pharmaceuticals.

[0048]

Example A-2 50 parts by weight of water was added to 30 parts by weight of fructose and 20 parts by weight of maltotetraose (sold by Hayashibara Biochemical Laboratory Co., Ltd.) and dissolved by heating. 60 this solution
After adjusting the temperature to pH 5.2 at 200C, 200 units of saccharified α-amylase (sold by Ueda Chemical Industry Co., Ltd.) was added per maltotetraosegram and allowed to act for 48 hours. The enzymatic reaction was stopped by keeping the reaction solution in a boiling water bath for 10 minutes.

This solution was decolorized with activated carbon according to a conventional method,
Desalted and purified with ion exchange resins (H type and OH type) and concentrated to give a syrup having a concentration of about 75% as a solid yield of about 9
Obtained at 5%. This product contained about 12% turanose per solid. This product has an elegant sweetness, an appropriate viscosity, and a moisturizing property as in the case of Example 1, and can be advantageously used for various compositions.

[0050]

Example A-3 0.15% of α-amylase (sold by Novo Co., trade name Tamarmeal) was added to starch milk having a concentration of 20% and liquefied by heating at 95 to 100 ° C.
The enzyme was inactivated by heating to obtain a liquefied solution of DE3. Fructose in an amount equal to that of starch as a solid substance was dissolved in this solution, and the temperature was adjusted to 55 ° C. and pH 5.3, and isoamylase (Hayashibara Biochemical Laboratories Co., Ltd.) was added at 10 g / starch.
0 unit and the same cyclomaltodextrin glucanotransferase as in Example A-1 were added at 300 units per gram of starch and reacted for 24 hours to inactivate the enzyme by heating.

After adding water to this solution to dilute it to a concentration of 25%, the temperature was maintained at 55 ° C. and pH 5.3, and 15 units of glucoamylase was added per dextrin glam for reaction for 16 hours. I made it live. This solution is
This solution containing about 35% of turanose per solid was purified and concentrated in the same manner as in Example A-1 to obtain syrup having a concentration of 75% with a solid yield of about 93%. This product is the product of Example A-1.
Similar to the above case, it has an elegant sweetness, an appropriate viscosity, a moisturizing property and the like, and can be advantageously used for various compositions.

[0052]

Example A-4 A solution containing turanose of about 35% based on the solid matter reacted and purified by the method of Example A-3 was used as a raw sugar solution. Column chromatography was carried out according to the method of Experiment 1 except that a salt-type strongly acidic cation exchange resin (trade name: CG 6000, Na type) sold by Organo Co., Ltd. was used as a fractionation resin in order to increase the turanose content of the solution. Then, the fraction containing high amounts of turanose was collected.

This high content liquid contained about 80% of turanose per solid matter. After this solution was concentrated to a concentration of about 76%, it was placed in a can of auxiliary crystals, about 2% of seed crystals were added, and the mixture was gradually cooled to obtain a maskit with a crystallization rate of about 45%. This mass kit was sprayed from a nozzle on the drying tower at a high pressure of 150 kg / cm ² .

Simultaneously with this, hot air of 85 ° C. is blown from the upper part of the drying tower to be collected on the transfer wire mesh conveyor provided at the bottom, and while warm air of 45 ° C. is sent from below the conveyor, it is collected on the wire mesh conveyor. The collected crystal powder was gradually moved to the outside of the drying tower and taken out. The crystal powder thus taken out was filled in a aging tower and aged for 10 hours while sending warm air, crystallization and drying were completed, and a honey-containing crystalline turanose powder was obtained. This product is
It has substantially no hygroscopicity, is easy to handle, and can be advantageously used as a sweetener, a taste improver, a quality improver, a stabilizer, and the like in various compositions such as food and drink, cosmetics, and pharmaceuticals.

[0055]

Example A-5 A solution containing about 20% turanose per solid matter prepared by the method of Example A-1 was added at a concentration of about 10%.
% To pH 4.6, 30 units of glucoamylase was added per dextrin grum, reacted for 16 hours, and then heated to inactivate the enzyme. This solution was decolorized with activated carbon, desalted with ion exchange resins (H type and OH type) and purified according to a conventional method, and concentrated to a concentration of about 45%. As a fractionation resin, a salt-type strongly acidic cation exchange resin (sold by Dow Chemical Co., product name Dowex 50W ×
Column chromatography was performed according to the method of Experiment 1 except that the Ca-type) was used to collect the fraction containing a large amount of turanose.

This high content liquid contained about 85% turanose per solid matter. This solution was concentrated to a concentration of about 85%, placed in an auxiliary crystal can, allowed to stand for 4 days at 20 ° C. to crystallize, solidify, then crushed with a cutting crusher, and dried to give a nectar-containing crystalline turanose powder. Obtained. This product, like the substance of Example A-4, does not exhibit substantially hygroscopicity, is easy to handle, and can be used in various compositions as a sweetener, a taste improver, a quality improver, a stabilizer, and the like. It can be used to advantage.

[0057]

Example B-1 Sweetener 1 part by weight of the crystalline turanose powder obtained by the method of Example A-4, 0.05 part by weight of α-glycosyl stepioside (sold by Toyo Seika Co., Ltd., trade name αG sweet). The parts were uniformly mixed and subjected to a granule molding machine to obtain a granular sweetener. This product has an excellent sweetness quality, has a sweetness that is about twice that of sucrose, and the calorie per sweetness is reduced to about 1/2 of that of sucrose.
The present sweetener is suitable as a low-calorie sweetener for sweetening low-calorie foods and drinks for obese people, diabetics and the like who have restricted caloric intake. In addition, the present sweetener is suitable for sweetening foods and beverages that suppress tooth decay because it produces less acid due to caries-inducing bacteria and less insoluble glucan.

[0058]

Example B-2: Hard candy 30 parts by weight of the syrup containing turanose obtained by the method of Example A-2 was heated and mixed with 100 parts by weight of a sucrose solution having a concentration of 55%, and the water content was reduced to less than 2% under reduced pressure. The mixture was heated and concentrated, and 1 part by weight of citric acid and an appropriate amount of lemon flavor and color were mixed and molded according to a conventional method to obtain a product.
This product is a high quality hard candy that has a crisp, good taste and does not cause sucrose to crystallize.

[0059]

[Example B-3] Strawberry jam 150 parts by weight of raw strawberry, 60 parts by weight of sucrose, maltose 2
0 parts by weight, 40 parts by weight of the syrup containing turanose obtained by the method of Example A-1, 5 parts by weight of pectin and 1 part of citric acid
Part by weight was boiled in a pan and bottled to obtain a product. This product is a jam with good flavor and color tone.

[0060]

Example B-4 Lactic Acid Beverage After sterilizing 10 parts by weight of skim milk by heating at 80 ° C. for 20 minutes,
The mixture was cooled to 40 ° C, 0.3 part by weight of a starter was added thereto, and the mixture was fermented at about 37 ° C for 10 hours. Next, this was homogenized, and then 4 parts by weight of the crystalline turanose powder obtained by the method of Example A-5, 1 part by weight of sucrose and 2 parts by weight of isomerized sugar syrup were added and sterilized at 70 ° C. This was cooled, an appropriate amount of fragrance was added, and bottled to obtain a product.
This product is a high-quality lactic acid beverage whose flavor and sweetness are in good harmony with sourness.

[0061]

Example B-5 Sweetened condensed milk 3 parts by weight of the syrup containing turanose obtained by the method of Example A-1 and 1 part by weight of sucrose were dissolved in 100 parts by weight of raw milk,
The product was sterilized by heating with a plate heater, then concentrated to a concentration of about 70%, and aseptically packed into a product. The product has a mild sweetness and a good flavor, and can be advantageously used for seasoning baby foods, fruits, coffee, cocoa, tea and the like.

[0062]

[Example B-6] Powdered juice 50 parts by weight of crystalline turanose powder obtained by the method of Example A-4, 10 parts by weight of sucrose, and 0% anhydrous citric acid were used with respect to 33 parts by weight of orange juice powder produced by spray drying. .65 parts by weight, malic acid 0.1 parts by weight, L-ascorbic acid 0.
1 part by weight, sodium citrate 0.1 part by weight, pullulan 0.
5 parts by weight and a proper amount of powdered fragrance were well mixed and stirred, pulverized into fine powder and charged into a fluidized bed granulator, and the exhaust air temperature 40
° C., and air volume per minute 150 meters ^3, which turanose-rich solution obtained by the method in Example A-4 to spray as a binder, granulated for 30 minutes, weighed and packaged to obtain a product.

The product is a powdered juice having a fruit juice content of about 30%. Further, this product had no off-taste or off-flavor, did not cause moisture absorption and solidification, and was stable for a long time.

[0064]

[Example B-7] 40 parts by weight of chocolate cocoa paste, 10 parts by weight of cocoa butter,
After mixing 50 parts by weight of the crystalline turanose powder obtained by the method of Example A-5 and passing through a refiner to reduce the particle size,
Put in a conche and knead at 50 ° C for 2 days. During this period, 0.5 part by weight of lecithin was added and thoroughly mixed and dispersed. Next, adjust the temperature to 31 ° C with a temperature controller, pour into the mold immediately before the butter hardens, and remove the foam with a vibrator.
It was solidified by passing through a 10 ° C. cooling tunnel for 20 minutes. This was die-cut and packaged to obtain a product.

This product has no hygroscopicity, has good color and gloss, has a good internal structure, melts smoothly in the mouth, and has an elegant sweetness and mellow flavor.

[0066]

Example B-8 Chewing Gum 3 parts by weight of a gum base are heated and melted to such an extent that it becomes soft,
To this, 4 parts by weight of sucrose and 3 parts by weight of crystalline turanose powder obtained by the method of Example A-5 were added, and an appropriate amount of flavor and colorant were mixed, and the mixture was kneaded by a roll according to a conventional method and molded, The product was packaged. This product is a chewing gum with good texture and flavor.

[0067]

[Example B-9] Custard cream 100 parts by weight of corn starch, 100 parts by weight of the syrup containing turanose obtained by the method of Example A-2, and maltose 8
Thoroughly mix 0 part by weight, 20 parts by weight of sucrose and 1 part by weight of salt, add 280 parts by weight of chicken egg and stir, gradually add 1000 parts by weight of boiled milk, and heat this to stir it. Subsequently, when the cornstarch was completely gelatinized and the whole became translucent, the heat was turned off, this was cooled, an appropriate amount of vanilla flavor was added, and the product was weighed, filled and packaged. This product has a smooth luster and is mildly sweet and delicious.

[0068]

[Example B-10] Uiro wax element 90 parts by weight of rice flour, 20 parts by weight of corn starch, 120 parts by weight of the crystalline turanose powder obtained by the method of Example A-4, and 4 parts by weight of pullulan are uniformly mixed to obtain Uiro. We manufactured the element. Knead Uironomoto, an appropriate amount of matcha and water,
This was put in a container and steamed for 60 minutes to produce matcha uiro. This product has good shine and mouth feel, and has a good flavor. In addition, the aging of starch is suppressed and the shelf life is good.

[0069]

Example B-11 Solid formulation for liquid foods Crystalline Turanose powder 500 obtained by the method of Example A-4.
Parts by weight, 270 parts by weight of powdered egg yolk, 209 parts by weight of skim milk powder, 4.4 parts by weight of sodium chloride, 1.8 potassium chloride
5 parts by weight, magnesium sulfate 4 parts by weight, thiamine 0.0
1 part by weight, 0.1 part by weight of sodium ascorbate, 0.6 part by weight of Vitamin E acetate and 0.04 part by weight of nicotinic acid amide were prepared, and 25 g of the mixture was filled in a moisture-proof laminated sachet. Then, heat sealing was performed to obtain a product. This product is used as a liquid food by dissolving one bag in about 150 to 300 mL of water, and is used orally or by a tube-like application method to the nasal cavity, stomach, intestines, etc.

[0070]

[Example B-12] Ointment plaster for treating wounds Crystalline Tranose powder 500 obtained by the method of Example A-4
To 50 parts by weight of methanol in which 3 parts by weight of iodine was dissolved was added and mixed, and further 200 parts by weight of 10% pullulan aqueous solution was added and mixed to obtain a plaster for trauma treatment showing moderate spread and adhesiveness. .. With this product, the healing period is shortened and the wound surface is healed cleanly.

[0071]

Example B-15 Sugar-coated tablet An uncoated tablet having a weight of 150 mg was used as a core agent, to which Example A-4 was applied.
A crystalline turanose powder obtained by the method of 40 parts by weight, pullulan (average molecular weight of 200,000) 2 parts by weight, water 30 parts by weight, talc 25 parts by weight, and a tableting solution having a tablet weight of 3 parts by weight are used. Sugar-coat until it is about 230 mg,
Next, 65 parts by weight of the same crystalline turanose and pullulan 1
Sugar coating was carried out using an overcoat liquid consisting of 1 part by weight and 34 parts by weight of water, and then further coated with a wax solution to obtain a sugar-coated tablet having an excellent glossy appearance. This product not only excels in workability when sugar-coated, but also in impact resistance, and maintains high quality for a long time.

[0072]

EFFECTS OF THE INVENTION As is clear from the above, turanose obtained by allowing cyclomaltodextrin-glucanotransferase or saccharified α-amylase to act on an aqueous solution containing starch and fructose has a high production rate and is isolated. , Easy to purify. Turanose is a disaccharide composed of glucose and fructose, and has an elegant and high-quality sweetness. In addition, it is used orally or parenterally, and is often metabolized without any concern about toxicity or side effects.

Although crystalline turanose is easily dissolved in water, it is virtually hygroscopic and easy to handle. Further, turanose has various properties such as osmotic pressure adjusting property, shaping property, luster imparting property, moisturizing property, viscosity, crystallization preventing property of other sugars, and non-fermentability. These properties can be advantageously utilized in the production of various compositions as a sweetener, a taste improver, a quality improver, a stabilizer and the like. Therefore, the establishment of the method for producing tulanose of the present invention and the use thereof has great industrial significance in the fields of food, cosmetics, pharmaceuticals, etc., which can be advantageously used.

[Brief description of drawings]

FIG. 1 shows a gas chromatogram of an enzyme reaction solution.

FIG. 2 shows an infrared absorption spectrum of crystalline turanose.

FIG. 3 shows a powder X-ray diffraction pattern of crystalline turanose.

Claims (5)

[Claims] 1. A method for producing turanose, which comprises reacting an aqueous solution containing starch and fructose with cyclomaltodextrin glucanotransferase or saccharified α-amylase to produce turanose, which is then collected. .. 2. The method for producing turanose according to claim 1, wherein glucoamylase is allowed to act together with cyclomaltodextrin glucanotransferase or saccharified α-amylase. 3. An aqueous solution containing starch and fructose is allowed to act on glucoamylase together with cyclomaltodextrin-glucanotransferase or saccharified α-amylase to produce turanose, which is separated and purified to have a high content of turanose. A method for producing turanose, which comprises preparing a liquid and further concentrating it to precipitate crystalline tranose for collection. 4. A solution containing a large amount of turanose is subjected to column chromatography using a salt type strongly acidic cation exchange resin,
The method for producing turanose according to claim 3, which is separated and purified. 5. A composition containing turanose obtained by allowing cyclomaltodextrin-glucanotransferase or saccharified α-amylase to act on an aqueous solution containing starch and fructose.